The electroreduction of aromatic aldehydes in aprotic solvents

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Abstract
The mechanism of electroreduction of aromatic aldehydes was investigated by cyclic voltammetry in dimethylformamide and acetonitrile in the presence of tetraethylammonium, potassium, and sodium perchlorates. It was found that the reaction products disappear in a dimerization reaction. Rate constants for the subsequent dimerization and association constants for ion pair intermediates were determined. The reactivity of the anion radicals initially formed decreases in the sequence: 9-anthraldehyde > benzaldehyde > 2-naphthaldehyde > 1-naphthaldehyde. The Hückel molecular orbital method was used to explain the reactivity sequence and the properties of the radical intermediates.

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